Triethylamine → 2-Acetoxy-3-methyl-3-(p-isobutylphenyl)acrylonitrile
Reaction equation
[C:1]([O:4][CH:5]([CH:8](Cl)[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=1)[C:6]#[N:7])(=[O:3])[CH3:2].[CH2:20](N(CC)CC)C>>[C:1]([O:4][C:5](=[C:8]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=1)[CH3:20])[C:6]#[N:7])(=[O:3])[CH3:2]Participants
Procedure
Following generally the procedure of Example 1, 3-methyl-3-pentyl-glycidonitrile (II) is treated with propionoyl bromide (III) in the presence of a catalytic amount of triethylamine hydrobromide to form 2-propionoyloxy-3-bromo-3-methyl-3-pentylpropionitrile (IV). The propionitrile (IV) is treated with triethylamine to form the 2-propionoyloxy-3-methyl-3-pentylacrylonitrile (V) enolacylate. The enol-acylate (V) is treated with aqueous potassium hydroxide to form the potssium 2-methylheptanoate salt (VI). The reaction mixture is treated with potassium hypochlorite to destroy cyanide ion in the mixture. The potassium salt (VI) is removed from the reaction mixture and diluted with a Skellysolve B-water mixture and then treated with 12N sulfuric acid to form the 2-methylheptanoic acid. Such acid is useful for modifying starches. (U.S.S.R Patent 348,576; C.A., 78 31775 w.).
Sources & evidence
- ORD record
- ord-1a3faffe95e34742b996d1eb0adb6f2a
- Source dataset
- uspto-grants-1976_10
- Patent number
- US03987094
Reaction notes
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